Price Reduced52$529,900
4 bd · 3 ba · 2,732 sqft
267 Runnymeade Drive, Winchester, KY
Jason Caudill · RE/MAX Creative Realty
Homes for Sale in Winchester, KY
Hide MapHomes for Sale in Winchester, KY
24 of 115 Listings
Price Reduced52$529,900
4 bd · 3 ba · 2,732 sqft
267 Runnymeade Drive, Winchester, KY
Jason Caudill · RE/MAX Creative Realty
74$385,000
3 bd · 2 ba · 1,344 sqft
2725 Goshen Road, Winchester, KY
Christa Joynt · Keller Williams Commonwealth
82$2,299,000
5 bd · 5 ba · 6,284 sqft
5039 Combs Ferry Road, Winchester, KY
Michael R Hilario · The Agency
Price Reduced32$189,000
3 bd · 1 ba · 1,152 sqft
32 Jackson Street, Winchester, KY
Dale Hatton · Dream Maker Realty, LLC
Price Reduced61$389,000
3 bd · 3 ba · 2,204 sqft
322 Calmes Boulevard, Winchester, KY
Darrell Tackett · Dream Maker Realty, LLC
Price Reduced55$379,000
4 bd · 2 ba · 3,306 sqft
351 Boone Avenue, Winchester, KY
James Woodrum · RE/MAX Creative, Winchester
Price Reduced52$419,000
3 bd · 2 ba · 2,942 sqft
1024 Flanagan Station Road, Winchester, KY
Brooke Martin · RO&CO Real Estate
64$524,900
3 bd · 3 ba · 2,514 sqft
275 Runnymeade Drive, Winchester, KY
Craig R Bridgewater · Bridgewater Real Estate
64$420,000
3 bd · 2 ba · 2,027 sqft
187 Hawthorne Drive, Winchester, KY
Christa Joynt · Keller Williams Commonwealth
46$749,900
3 bd · 3 ba · 2,735 sqft
2180 Big Stoner Road, Winchester, KY
Ashley Barreto · Indigo & Co
Price Reduced35$299,900
5 bd · 2 ba · 2,082 sqft
128 Cherokee Drive, Winchester, KY
Tyler A Hurst · Oak & Acre
Price Reduced50$209,500
3 bd · 2 ba · 1,200 sqft
491 Hidden Hills Way, Winchester, KY
Robin Trimble · HomeFirst Real Estate
Price Reduced64$379,000
4 bd · 3 ba · 1,978 sqft
107 Hibiscus Lane, Winchester, KY
Christa Joynt · Keller Williams Commonwealth
Price Reduced60$699,000
2 bd · 3 ba · 2,361 sqft
455 Davis Lane, Winchester, KY
Dale Hatton · Dream Maker Realty, LLC
Price Reduced27$146,900
3 bd · 2 ba · 1,680 sqft
65 Fitch Avenue, Winchester, KY
Mila J Ensor · Ensor Real Estate, LLC
Price Reduced33$357,000
3 bd · 3 ba · 1,945 sqft
309 Gallahadion Court, Winchester, KY
Michelle R Blackburn · RE/MAX Creative, Winchester
Price Reduced16$124,500
2 bd · 1 ba · 876 sqft
122 Callaway Street SE Callaway Street, Winchester, KY
Darrell Tackett · Dream Maker Realty, LLC
22$665,000
3 bd · 3 ba · 2,643 sqft
414 Alexis Way, Winchester, KY
Shane T Underwood · Keller Williams Commonwealth
3$645,000
4 bd · 3 ba · 2,526 sqft
106 Bella Shae Way, Winchester, KY
Shane T Underwood · Keller Williams Commonwealth
3$825,000
3 bd · 3 ba · 2,995 sqft
111 Bella Shae Way, Winchester, KY
Shane T Underwood · Keller Williams Commonwealth
4$635,000
4 bd · 3 ba · 2,537 sqft
422 Alexis Way, Winchester, KY
Shane T Underwood · Keller Williams Commonwealth
4$625,000
3 bd · 3 ba · 2,405 sqft
424 Alexis Way, Winchester, KY
Shane T Underwood · Keller Williams Commonwealth
9$785,000
4 bd · 3 ba · 2,476 sqft
425 Alexis Way, Winchester, KY
Shane T Underwood · Keller Williams Commonwealth
Price Reduced35$258,900
2 bd · 1 ba · 849 sqft
955 Right Angle Road, Winchester, KY
Rhett Hughes · WTC Realty LLC
Imagine MLS (Bluegrass REALTORS)Source: HJN community data
August 2026 · This period is still settling
Selling at 98.2% of asking price
Buyers here are paying below asking. MLS · 32 sales · as of Aug 31, 2026